CH253178A - Process for the preparation of an acylated, aliphatic aminocarboxamide. - Google Patents
Process for the preparation of an acylated, aliphatic aminocarboxamide.Info
- Publication number
- CH253178A CH253178A CH253178DA CH253178A CH 253178 A CH253178 A CH 253178A CH 253178D A CH253178D A CH 253178DA CH 253178 A CH253178 A CH 253178A
- Authority
- CH
- Switzerland
- Prior art keywords
- acylated
- preparation
- aliphatic
- aminocarboxamide
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title description 3
- 125000001931 aliphatic group Chemical group 0.000 title description 3
- 238000009835 boiling Methods 0.000 claims description 5
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- FMSSTWGVVMAWCY-UHFFFAOYSA-N ClO.CNC Chemical compound ClO.CNC FMSSTWGVVMAWCY-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäureamids. Gegenstand des vorliegenden Zusatzpaten tes ist ein Verfahren zur Darstellung eines acylierten, aliphatischen Aminocarbonsäure- amids. Das, Verfahren ist dadurch gekenn zeichnet, dass N-Propionyl-a-amino-n-butter- säuredimethylamid propyliert wird.
Das N-Propionyl-a-(n-propylamino)-n-but- tersäuredimethylamid der Formel
EMI0001.0015
bildet eine farblose Flüssigkeit vom Siede punkt, 119 bis 120 unter 0,2 mm. Die neue Verbindung soll therapeutische Verwendung f roden.
<I>Beispiel:</I> 28,8 Teile a-Amino-n-buttersäuredimethyl- amid werden in 200 Teilen Äther gelöst und rmter Rühren und Kühlen 9,4 Teile Pro pionylchlorid zugetropft. Naeh 2stündigem Rühren wird vom a-Amino-n-buttersäure- dimethylamid-chlorhydrat filtriert, vom Äther durch Destillation befreit und das Produkt fraktioniert:
Siedepunkt 170 bis 172 unter 0,2 mm. 17,2 Teile des erhaltenen N-Pro- pionyl - o: -amino-n-buttersäuredimethylamids in 200 Teilen Xylol worden mit 4 Teilen Na; triumamid einige Zeit zum Sieden erhitzt. Nach dem Abkühlen wird mit 25 Teilen Propylbromid versetzt und im Druckgefäss auf 150 bis 160 erhitzt. Das Reaktionspro dukt wird mit gesättigter Kalilauge durch geschüttelt und die Xylollösung abgetrennt.
Nach dem Abdestillieren des Xylols wird der Rückstand im Hochvakuum rektifiziert. Die neue Verbindung zeigt den Siedepunkt 119 bis 120 unter 0,2 mm und ist leicht löslich in Wasser und organischen Lösungsmitteln.
process for the preparation of an acylated, aliphatic aminocarboxamide. The present additional patent is a process for the preparation of an acylated, aliphatic aminocarboxylic acid amide. The process is characterized in that N-propionyl-a-amino-n-butyric acid dimethylamide is propylated.
The N-propionyl-a- (n-propylamino) -n-but-tersäuredimethylamid of the formula
EMI0001.0015
forms a colorless liquid with a boiling point of 119 to 120 below 0.2 mm. The new compound is intended to have therapeutic uses.
<I> Example: </I> 28.8 parts of a-amino-n-butyric acid dimethyl amide are dissolved in 200 parts of ether and 9.4 parts of propionyl chloride are added dropwise with stirring and cooling. After stirring for 2 hours, the a-amino-n-butyric acid dimethylamide chlorohydrate is filtered, the ether is removed by distillation and the product is fractionated:
Boiling point 170 to 172 below 0.2 mm. 17.2 parts of the obtained N-propionyl-o: -amino-n-butyric acid dimethylamide in 200 parts of xylene with 4 parts of Na; triumamid heated to boiling for some time. After cooling, 25 parts of propyl bromide are added and the mixture is heated to 150 to 160 in a pressure vessel. The reaction product is shaken through with saturated potassium hydroxide solution and the xylene solution is separated off.
After the xylene has been distilled off, the residue is rectified in a high vacuum. The new compound has a boiling point of 119 to 120 below 0.2 mm and is easily soluble in water and organic solvents.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH244952T | 1942-12-18 | ||
| CH253178T | 1942-12-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH253178A true CH253178A (en) | 1948-02-15 |
Family
ID=25729004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH253178D CH253178A (en) | 1942-12-18 | 1942-12-18 | Process for the preparation of an acylated, aliphatic aminocarboxamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH253178A (en) |
-
1942
- 1942-12-18 CH CH253178D patent/CH253178A/en unknown
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